The overall goal of our laboratory is the development of new methodology and strategy-level insights of value to organic synthesis. These advances are then applied to the assembly of complex, biologically active synthetic targets. We strive to bring these advances to bear in understanding structure-activity relationships (SAR) of complex small molecules and carbohydrate-based constructs. Our research program for CA28824 can be divide into three general categories. In the first, we are focused on the total synthesis of structurally interesting natural products of biological value. Some of the targets that we have selected for the upcoming grant period include: spiculoic acid, lyconadin, and pluraflavin. In addition, we have an ongoing program devoted to the preparation of fully synthetic, carbohydrate-based antitumor vaccines. In the upcoming grant period, we will be targeting a hexavalent vaccine construct as well as a "cluster of clusters" vaccine, which we hope will have great value in treating prostate cancer. We also hope to complete the synthesis of a clustered fucosyl-GM1 vaccine construct, targeting small cell lung carcinoma. Finally, a third subprogram is focused on the development of methods to allow for the preparation of fully synthetic glycoproteins. A long-term goal of this program is the preparation of homogeneous erythropoietin.